Synthesis of a 6‑CF3‑Substituted 2‑Amino-dihydro-1,3-thiazine β‑Secretase Inhibitor by N,N‑Diethylaminosulfur Trifluoride-Mediated Chemoselective Cyclization

The synthesis of a 6-CF3-substituted 2-amino-dihydro-1,3-thiazine via N,N-diethylaminosulfur trifluoride (DAST)-mediated cyclization of N-hydroxypropyl thiourea 6 is described. This reaction gave 6-CF3-1,3-thiazine 7 with high chemical yield and chemoselectivity, suppressing the common byproduct of...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-04, Vol.84 (8), p.4893-4897
Main Authors: Oguma, Takuya, Anan, Kosuke, Suzuki, Shinji, Hisakawa, Shinya, Takada, Akihiro, Ogawa, Masayoshi, Kusakabe, Ken-ichi
Format: Article
Language:English
Online Access:Get full text
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Summary:The synthesis of a 6-CF3-substituted 2-amino-dihydro-1,3-thiazine via N,N-diethylaminosulfur trifluoride (DAST)-mediated cyclization of N-hydroxypropyl thiourea 6 is described. This reaction gave 6-CF3-1,3-thiazine 7 with high chemical yield and chemoselectivity, suppressing the common byproduct of oxazine 8. This new protocol enabled access to 6-CF3-substituted 1,3-thiazine β-secretase inhibitor 2.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02179